tert-butyl (S)-2-(((benzyloxy)carbonyl)amino)but-3-enoate | 117751-86-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (S)-2-(((benzyloxy)carbonyl)amino)but-3-enoate
• 英文别名: 2(S)-tert-butyl 2-N-benzyloxycarbonylamino-3-butenoate；tert-butyl (2S)-N-benzyloxycarbonyl-2-vinyl-glycine；tert-butyl 2-(S)-benzyloxycarbonylaminobut-3-enoate；N-Cbz-L-vinylglycine tert-butyl ester；tert-butyl (2S)-2-(phenylmethoxycarbonylamino)but-3-enoate
• CAS: 117751-86-7
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: GZGOTERLWIWBKL-ZDUSSCGKSA-N

物化性质

• 沸点：
  414.4±45.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-(((benzyloxy)carbonyl)amino)but-3-enoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以95%的产率得到(S)-N-(benzyloxycarbonyl)vinylglycine
  参考文献：
  名称：

  [EN] RIP1K INHIBITORS
  [FR] INHIBITEURS DE RIP1K

  摘要：

  披露的是激酶抑制化合物，例如受体相互作用蛋白-1（RIP1）激酶抑制化合物，以及包含此类抑制化合物的药物组合物和组合。所披露的化合物、药物组合物和/或组合可用于治疗或预防与激酶相关的疾病或状况，尤其是与RIP1相关的疾病或状况。

  公开号：

  WO2021203011A1
• 作为产物：
  描述：

  (S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester 在 N-甲基吗啉 、 三丁基膦 、 KSeCN-2-NO₂C₆H₄ 、 氯甲酸乙酯 作用下， 生成 tert-butyl (S)-2-(((benzyloxy)carbonyl)amino)but-3-enoate
  参考文献：
  名称：

  细菌Glu-tRNA（Gln）酰胺基转移酶的谷氨酰胺-γ-硼酸盐抑制剂。

  摘要：

  合成了谷氨酰胺-γ-硼酸酯（1）的类似物，作为细菌Glu-tRNA（Gln）酰胺基转移酶（Glu-AdT）的基于机理的抑制剂，并被设计为与该酶的谷氨酰胺酶活性所需的假定的催化丝氨酸亲核试剂结合。尽管1提供了有效的酶抑制作用，但结构活性研究显示，可以维持活性的耐受化学变化范围很小。然而，最有效的酶抑制剂对需要Glu-AdT的生物的生长抑制似乎证实了基于机制的Glu-AdT抑制剂设计是抗菌剂开发的一种方法。

  DOI：

  10.1016/s0960-894x(01)00499-1

文献信息

• Synthesis of 2'-epi-distichonic acid A, an iron-chelating amino acid derivative.
  作者：TAKASHI TASHIRO、SHINJI FUSHIYA、SHIGEO NOZOE

  DOI：10.1248/cpb.36.893

  日期：——

  2'-epi-Distichonic acid A (4b), an iron-chelating amino acid derivative was synthesized starting from L-vinylglycine epoxide (6b). Reaction of 6b with glycine ester 17 afforded a β-hydroxy amino acid derivative (18). Reductive coupling of 21 derived from 18 with L-malic-β-semialdehyde (25) gave 2'-epi-distichonic acid A (4b) after deprotection.

  从L-乙烯基甘氨酸环氧化物（6b）出发，合成了一种铁螯合氨基酸衍生物2'-表双歧酸A（4b）。6b与甘氨酸酯17反应得到β-羟基氨基酸衍生物（18）。由18衍生的21与L-苹果酸-β-半醛（25）进行还原偶联，去保护后得到2'-表双歧酸A（4b）。
• The synthesis of diaminopimelic acid containing peptidoglycan fragments using metathesis cross coupling
  作者：Abhijit Roy Chowdhury、Geert-Jan Boons

  DOI：10.1016/j.tetlet.2005.01.062

  日期：2005.3

  protected diaminopimelic acid (DAP), a component of peptidoglycan of Gram-negative bacteria, was prepared by a metathesis cross coupling between properly protected allyl and vinyl glycine derivatives using Grubb’s second-generation catalyst followed by reduction of the double bond of the resulting compound. The DAP derivatives were used in the solution- and polymer-supported synthesis of biological active peptides

  正确保护的二氨基庚二酸（DAP）是革兰氏阴性细菌的肽聚糖的一种成分，它是通过使用第二代催化剂Grubb在适当保护的烯丙基和乙烯基甘氨酸衍生物之间进行易位交叉偶联，然后还原所得化合物的双键来制备的。DAP衍生物用于溶液和聚合物支持的生物活性肽合成中。
• Suzuki-Miyaura cross-coupling reaction of monohalopyridines and l-aspartic acid derivative
  作者：Ayame Mikagi、Dai Tokairin、Toyonobu Usuki

  DOI：10.1016/j.tetlet.2018.11.038

  日期：2018.12

  cross-coupling reaction of halogenated pyridines and a borated l-aspartic acid derivative was conducted. The reactivity of chloro-, bromo-, and iodo-pyridines with substituents at the C2, C3, and C4 positions was investigated. Electron density of halogenated pyridines was also estimated by density functional theory (DFT) calculations. The order of experimental yield of halogen substituents was Br > I >> Cl

  进行了卤代吡啶与硼酸化的1-天冬氨酸衍生物的Suzuki-Miyaura交叉偶联反应。研究了氯，溴和碘吡啶在C2，C3和C4位置具有取代基的反应性。卤代吡啶的电子密度也通过密度泛函理论（DFT）计算来估算。卤素取代基的实验产率顺序为：Br> I >> Cl，C3> C2，C4，而DFT结果表明反应顺序为：I >> Br，Cl和C4> C2，C3。优化的实验条件（3-溴吡啶）定量提供了偶联产物。
• Palladium(0) catalysed and copper(i) promoted reactions of the secondary zinc reagent derived from L-threonine
  作者：Ian Wilson、Richard F. W. Jackson

  DOI：10.1039/b208667k

  日期：2002.12.19

  C-3 epimeric secondary zinc reagents 2a/b were prepared from either diastereoisomeric iodide 3a or 3b using DMF as solvent, and characterised by 1H NMR methods. Palladium catalysed cross couplings and copper promoted allylations yielded protected β-methyl substituted amino acids.

  C-3 立体异构的二级锌试剂 2a/b 是通过使用 DMF 作为溶剂，从非对映体碘化物 3a 或 3b 制备的，并通过 1H NMR 方法进行了表征。钯催化的交叉偶联反应和铜促进的烯丙基化反应获得了保护的 β-甲基取代氨基酸。
• Prodrug Forms of <i>N</i>-[(4-Deoxy-4-amino-10-methyl)pteroyl]glutamate-γ-[ψP(O)(OH)]-glutarate, a Potent Inhibitor of Folylpoly-γ-glutamate Synthetase: Synthesis and Hydrolytic Stability
  作者：Yan Feng、James K. Coward

  DOI：10.1021/jm050871p

  日期：2006.1.1

  Ester prodrugs of the phosphinate pseudopeptide N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-gamma-[psi P(0)(OH)]-glutarate (1a) were synthesized. H-phosphinic acids derived from N-Cbz vinyl glycine esters were converted to the desired pseudopeptides by Michael addition to alpha-methyleneglutarate esters. Pivaloyloxymethyl (POM) ester moieties were incorporated in both the N-terminal and C-terminal fragments prior to formation of either C-P bond. N-Alkylation of the corresponding amides derived from p-(N-methyl)aminobenzoic acid with 2,4-diamino-6-(bromomethyl)pteridine gave the target compounds. POM esters of methotrexate and the corresponding gamma-glutamyl conjugate were also synthesized using the same strategy. All prodrugs were evaluated in Chinese hamster ovary cells. Although the pseudopeptide prodrugs were ineffective, prodrugs of methotrexate and the corresponding gamma-glutamyl conjugate were equipotent with the parent compounds. Stability of the prodrugs was investigated in both phosphate buffer and cell line medium to provide a rationale for the observed biological data.